Rpi not booting after host restart

Hi!
I am running HAOS on RPi 5 with an SSD connected to it. It is connected to my router via ethernet.

After I choose an option to reboot the system, HA does not start. I checked and my RPi is not online either but maybe it would not show as online if the HAOS is not running?

When this happens, I need to power-cycle the RPi and the HAOS starts. Is this normal? Is this a matter of choosing the right setting somewhere?
When I travel, I would like to have an automation that would ask me if I want to restart the host. If I don’t reply within a given period of time, it would likely mean that something went wrong and the host would reboot. As a side note I would do the same with the router first since lack of internet connection is a more likely scenario.

Thank you!

Can you attach a display and see what is shown when the issue occurs?

This automation part is hard because ha is not working.
In the past I have thought about such a solution. You could use a Shelly plug s with esphome and check if you can reach ha. If not for x amount of time you can power cycle.

But back then I found the root cause of the crash and I hope you will do too. Because fixing that is way better.

Is your SSD attached to a powered USB hub? Same thing happens to me because the hub is back-powering the pi preventing complete shutdown.

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Thank you for both replies. It makes sense about HA not working so then automation not working either. Luckily, I do not have any issues, I wanted to have something like this just in case.
Good point about a smart plug. I thought about it too both for HA and for the router.

About the USB hub, no, the SSD is connected directly to the RPi. I think it is an USB to SATA adapter.

I was just curious if there is a parameter or a setting I need to change to start the host and HA after the host reboot and why it starts after power cycling and not the reboot.

It is a known issue:

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